How to Be More Comfortable in Your Clothes

If your clothes are comfortable—like, pajama-level comfortable—you will live for the cold, love getting dressed up, and look forward to long flights. So yeah, it’s definitely worth a little bit of consideration. But before you go reaching for seven pairs of tailored sweatpants, try these tricks and tips for your everyday wardrobe. What you’ll find is that comfort is all about fit, fabric and versatility. Master those three elements and you’ll also be the most confident guy in the room.

Take It Easy

Stretch Your Shoes a Bit

We know it’s tempting to sprint out of the store wearing your brand-new shoes but for the sake of your feet, don’t. Have them stretched by your shoe repair shop or stretch them yourself with inserts or thick socks. Blisters are not worth the instant gratification you get from wearing them straight away.

Have an Undershirt On Hand

You don’t have to wear an undershirt religiously but when a fabric is stiff or you’re prone to sweating, it can really save the day. Remember that not all T-shirts are appropriate undershirts. You want a slim cut, deep v neckline and 100% cotton fabrication.

Beware of Vanity Sizing

Not only are XS through XL not to be trusted but actual waist sizes can differ from brand to brand too. Given that, always try on two sizes to make sure you’re getting the perfect fit. If you’re buying online, read the item description and look to the exact measurements for clues on what to go with.

Buy Breathable Fabrics

Natural fiber fabrics like cotton and wool allow moisture to escape while synthetics like polyester and acetate do not. In fact, the stifling quality of synthetic fabrics will make you sweat and stink even more. In other words, think twice before buying all your clothes at high-street stores.

Wash Your Damn Jeans

Good-quality denim can stand a few washes so there’s no need to be so extreme about breaking in raw jeans. Cold rinse and flat dry your jeans every 6 weeks or so and the breaking-in process will be infinitely more comfortable (and way less gross) than trying to go wash-free.

Always Dress in Layers

That whole double jackets thing we’ve been telling you about isn’t just for looks—dressing in layers pretty much guarantees comfort. From your freezing-as-hell office to the sweaty, overcrowded bar you frequent after work, an outfit with options will keep you comfortable no matter what life throws your way.

Pay Attention to Lining

The fabric used to line your clothes—or lack thereof—can make a big difference in how comfortable you feel in them. Look for silks, satins and cashmere-lined garments and avoid synthetics and unlined items unless the fabric itself is quite luxurious. When it comes to suits, lining that isn’t fused or glued directly to the suit fabric is a sign of good quality.

Tailor (Almost) Everything

Find a tailor you like (bonus points if he’s got some good stories to tell) and make visiting him part of your weekly or monthly routine, just like dropping off your dry cleaning. Clothes that fit you well not only look great, they feel infinitely better than those that tug, pull, or pool on you in weird ways.

Invest in Staying-In Clothes

From cashmere socks and blankets to proper pajamas, spending a couple of bucks on luxurious downtime clothes will make changing after work a euphoric experience and safeguard you against a variety of uncomfortable travel scenarios. Plus, you never know who will drop by—might as well look your best.

Embrace the Unstructured Blazer

Layering around a perfectly cut, structured blazer can be tricky in the winter, which is why it’s good to have an unstructured jacket on hand for days when you want to look smart without freezing to death. The jacket’s softer fabrication and slouchier cut is infinitely more comfortable than your go-to suit jacket.

We know it’s tempting to sprint out of the store wearing your brand-new shoes but for the sake of your feet, don’t. Have them stretched by your shoe repair shop or stretch them yourself with inserts or thick socks. Blisters are not worth the instant gratification you get from wearing them straight away.

Stretch Your Shoes a Bit

You don’t have to wear an undershirt religiously but when a fabric is stiff or you’re prone to sweating, it can really save the day. Remember that not all T-shirts are appropriate undershirts. You want a slim cut, deep v neckline and 100% cotton fabrication.

Have an Undershirt On Hand

Not only are XS through XL not to be trusted but actual waist sizes can differ from brand to brand too. Given that, always try on two sizes to make sure you’re getting the perfect fit. If you’re buying online, read the item description and look to the exact measurements for clues on what to go with.

Beware of Vanity Sizing

Natural fiber fabrics like cotton and wool allow moisture to escape while synthetics like polyester and acetate do not. In fact, the stifling quality of synthetic fabrics will make you sweat and stink even more. In other words, think twice before buying all your clothes at high-street stores.

Buy Breathable Fabrics

Good-quality denim can stand a few washes so there’s no need to be so extreme about breaking in raw jeans. Cold rinse and flat dry your jeans every 6 weeks or so and the breaking-in process will be infinitely more comfortable (and way less gross) than trying to go wash-free.

Wash Your Damn Jeans

That whole double jackets thing we’ve been telling you about isn’t just for looks—dressing in layers pretty much guarantees comfort. From your freezing-as-hell office to the sweaty, overcrowded bar you frequent after work, an outfit with options will keep you comfortable no matter what life throws your way.

Always Dress in Layers

The fabric used to line your clothes—or lack thereof—can make a big difference in how comfortable you feel in them. Look for silks, satins and cashmere-lined garments and avoid synthetics and unlined items unless the fabric itself is quite luxurious. When it comes to suits, lining that isn’t fused or glued directly to the suit fabric is a sign of good quality.

Pay Attention to Lining

Find a tailor you like (bonus points if he’s got some good stories to tell) and make visiting him part of your weekly or monthly routine, just like dropping off your dry cleaning. Clothes that fit you well not only look great, they feel infinitely better than those that tug, pull, or pool on you in weird ways.

Tailor (Almost) Everything

From cashmere socks and blankets to proper pajamas, spending a couple of bucks on luxurious downtime clothes will make changing after work a euphoric experience and safeguard you against a variety of uncomfortable travel scenarios. Plus, you never know who will drop by—might as well look your best.

Invest in Staying-In Clothes

Layering around a perfectly cut, structured blazer can be tricky in the winter, which is why it’s good to have an unstructured jacket on hand for days when you want to look smart without freezing to death. The jacket’s softer fabrication and slouchier cut is infinitely more comfortable than your go-to suit jacket.